CA2797406C - Polymeres conjugues multicolores avec etat oxyde a transmission elevee - Google Patents

Polymeres conjugues multicolores avec etat oxyde a transmission elevee Download PDF

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CA2797406C
CA2797406C CA2797406A CA2797406A CA2797406C CA 2797406 C CA2797406 C CA 2797406C CA 2797406 A CA2797406 A CA 2797406A CA 2797406 A CA2797406 A CA 2797406A CA 2797406 C CA2797406 C CA 2797406C
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units
unit
arylalkyl
amino
copolymer
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CA2797406A1 (fr
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John R. Reynolds
Pengjie Shi
Jianguo Mei
Chad Martin Amb
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University of Florida Research Foundation Inc
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University of Florida Research Foundation Inc
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/122—Copolymers statistical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/414—Stille reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/54—Physical properties electrochromatic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1491—Heterocyclic containing other combinations of heteroatoms
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect
    • G02F1/1514—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
    • G02F1/1516—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising organic material
    • G02F1/15165—Polymers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

Des modes de réalisation de l'invention concernent des copolymères conjugués statistiques comprenant une pluralité d'un ou plusieurs motifs de répétition donneurs (D) différents et une pluralité d'au moins un motif de répétition accepteur (A). Au moins l'un des motifs D a un substituant solubilisant, statistiquement une partie des motifs de répétition A sont séparés les uns des autres par un seul motif D et une pluralité de motifs A sont adjacents à un des motifs D ayant les substituants solubilisants. Les copolymères conjugués statistiques sont noirs ou colorés à l'état neutre et ont une transmission élevée dans l'état oxydé. Les copolymères conjugué statistiques ont la structure -[(D)xA]n-, où x > 1 et n(x+1) = 10 ou la structure - [(DA)x-(D'A)y]n-, où D représente un motif D substitué et D' représente un autre motif D et où x = 1, y = 1 et 2n(x+y) = 10. D'autres modes de réalisation de l'invention concernent la formation des copolymères conjugués statistiques -[(D)xA]n- ou -[(DA)x-(D'A)y]n- par polymérisation par condensation entre des monomères contenant des groupes réactifs complémentaires.
CA2797406A 2010-05-21 2011-05-19 Polymeres conjugues multicolores avec etat oxyde a transmission elevee Expired - Fee Related CA2797406C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US34709110P 2010-05-21 2010-05-21
US61/347,091 2010-05-21
PCT/US2011/037138 WO2012021195A2 (fr) 2010-05-21 2011-05-19 Polymères conjugués multicolores avec état oxydé à transmission élevée

Publications (2)

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CA2797406A1 CA2797406A1 (fr) 2012-02-16
CA2797406C true CA2797406C (fr) 2018-06-26

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CA2797406A Expired - Fee Related CA2797406C (fr) 2010-05-21 2011-05-19 Polymeres conjugues multicolores avec etat oxyde a transmission elevee

Country Status (8)

Country Link
US (1) US8450449B2 (fr)
EP (1) EP2571920A4 (fr)
JP (1) JP5748843B2 (fr)
CN (1) CN102906153A (fr)
BR (1) BR112012029584A2 (fr)
CA (1) CA2797406C (fr)
RU (1) RU2012151578A (fr)
WO (1) WO2012021195A2 (fr)

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KR101259865B1 (ko) * 2011-11-21 2013-05-02 광주과학기술원 저밴드갭의 공중합체 및 이의 제조방법
EP2875033B8 (fr) * 2012-07-23 2019-09-11 The University of Connecticut Copolymères électrochromes à partir de précurseurs, leur procédé de fabrication et leur utilisation
US10323178B2 (en) 2014-05-16 2019-06-18 The University Of Connecticut Color tuning of electrochromic devices using an organic dye
WO2016081787A2 (fr) 2014-11-19 2016-05-26 Biltmore Technologies, Inc. Système de revêtement à couleur contrôlée et changement d'opacité
CN105504233B (zh) * 2016-01-04 2018-09-07 京东方科技集团股份有限公司 电致变色聚合物及其制备方法和包含其的组件
US9975989B2 (en) 2016-05-04 2018-05-22 Furcifer Inc. Multicolored electrochromic polymer compositions and methods of making and using the same
CN107880253B (zh) * 2017-11-23 2019-09-20 深圳市光羿科技有限公司 一种黑色电致变色高分子材料及其制备方法和应用
CN111527574B (zh) * 2017-12-25 2022-12-09 昭和电工株式会社 固体电解电容器制造用分散液组合物和固体电解电容器的制造方法
CN111217990A (zh) * 2020-01-20 2020-06-02 西安交通大学 基于不同取代吡嗪受体单元的d-a共聚物给体材料及应用
WO2023063954A1 (fr) * 2021-10-14 2023-04-20 Ambilight Inc. Polymère électrochrome ayant un dérivé de pyrrole et du thiophène
US12529932B2 (en) 2022-02-09 2026-01-20 Ambilight Inc High transparency electrochromic polymers
US12372842B2 (en) 2022-02-09 2025-07-29 Ambilight Inc High transparency electrochromic polymers
US12174505B2 (en) 2022-02-09 2024-12-24 Ambilight Inc High transparency electrochromic polymers
US11879098B2 (en) 2022-02-09 2024-01-23 Ambilight Inc. High transparency electrochromic polymers
US11874578B2 (en) 2022-02-09 2024-01-16 Ambilight Inc. High transparency electrochromic polymers
CN118660919A (zh) * 2022-02-16 2024-09-17 金泰克斯公司 电致变色嵌段共聚物和用此类共聚物制成的装置

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US7256923B2 (en) * 2001-06-25 2007-08-14 University Of Washington Switchable window based on electrochromic polymers
US6791738B2 (en) * 2001-11-21 2004-09-14 University Of Florida Electrochromic polymers and polymer electrochromic devices
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Publication number Publication date
JP2013526648A (ja) 2013-06-24
EP2571920A4 (fr) 2014-01-29
JP5748843B2 (ja) 2015-07-15
US20110288253A1 (en) 2011-11-24
US8450449B2 (en) 2013-05-28
BR112012029584A2 (pt) 2019-09-24
CN102906153A (zh) 2013-01-30
RU2012151578A (ru) 2014-06-27
CA2797406A1 (fr) 2012-02-16
WO2012021195A3 (fr) 2012-04-26
EP2571920A2 (fr) 2013-03-27
WO2012021195A2 (fr) 2012-02-16

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